The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 11-Bromoundecanoic acid( cas:2834-05-1 ) is researched.Electric Literature of C11H21BrO2.Pradhan, Tapas R.; Lee, Hae Eun; Gonzalez-Montiel, Gisela A.; Cheong, Paul Ha-Yeon; Park, Jin Kyoon published the article 《Highly Chemoselective Esterification from O-Aminoallylation of Carboxylic Acids: Metal- and Reagent-Free Hydrocarboxylation of Allenamides》 about this compound( cas:2834-05-1 ) in Chemistry – A European Journal. Keywords: trans acyloxyenamide preparation regioselective chemoselective diastereoselective green chem; allenamide carboxylic acid hydrocarboxylation aminoallylation; (E)-enamides; Brønsted acid; carboxylic acids; linear selective; metal-free. Let’s learn more about this compound (cas:2834-05-1).
Metal-free hydrocarboxylation of allenamides RCH=C=CH2 (R = N-benzyl(4-methylbenzene)sulfonamide, (methoxycarbonyl)(naphthalen-1-yl)aminyl, 2-oxo-1,3-oxazolidin-3-yl, etc.) with various functionalized carboxylic acids R1C(O)OH (R1 = Me, Ph, 1-(4-nitrophenyl)ethyl, 6-chloroimidazo[1,2-a]pyridin-3-yl, etc.) was achieved with complete regio- and stereocontrol (>49:1). This environmentally compatible transformation affords γ-acyloxyenamides RCH=CHCH2OC(O)R1 with exclusive E-selectivity. Electron rich, electron poor, aliphatic, aryl, and heterocyclic carboxylic acids all gave excellent yields (avg. 89%, 47 examples). The synthetic potential of this transformation in the late-stage modification of complex natural carboxylic acids and simple modification of the products to three-carbon synthons with ample opportunity for further diversification were demonstrated. DFT studies revealed that the reaction occurs in a stepwise manner through the intermediacy of a conjugated iminium species, which is rapidly captured by the carboxylate ion, resulting in the observed linear selectivity.
《Highly Chemoselective Esterification from O-Aminoallylation of Carboxylic Acids: Metal- and Reagent-Free Hydrocarboxylation of Allenamides》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(11-Bromoundecanoic acid)Electric Literature of C11H21BrO2.
Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI